2-methylpropane-2-sulfinic acid [1-(2-methyl-1-ylphenyl)ethylidene]amide | 1208989-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methylpropane-2-sulfinic acid [1-(2-methyl-1-ylphenyl)ethylidene]amide
• 英文别名: (R_S)-N-(o-methylbenzylidene)-2-methyl-2-propanesulfinamide；(Rs)-2-methyl-N-(2-methylbenzylidene)propane-2-sulfinamide；(R)-2-methyl-N-[(2-methylphenyl)methylidene]propane-2-sulfinamide
• CAS: 1208989-34-7
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: HXORHDQDAIXGBN-OAHLLOKOSA-N

物化性质

• 沸点：
  355.0±35.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylpropane-2-sulfinic acid [1-(2-methyl-1-ylphenyl)ethylidene]amide 在 sodium perborate tetrahydrate 、 1,2-双(二苯基膦基)苯 、 copper(I) bromide 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 (R)-N-((R)-2-hydroxy-1-(o-tolyl)ethyl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Diborylmethane的铜催化的立体选择性加成到ñ -叔-Butanesulfinyl醛亚胺：β-Aminoboronates的合成

  摘要：

  我们已经开发的高度化疗和立体选择性烷基化ñ -叔-butanesulfinyl亚胺与diborylmethane。在无金属条件下添加二硼烷基甲烷显示出较差的非对映选择性，而铜催化剂和二齿膦配体的使用显着增强了非对映选择性，从而以高收率提供了手性β-氨基硼酸酯。根据立体化学结果，我们建议反应可能通过硼螯合六元椅状过渡态进行。

  DOI：

  10.1021/acs.orglett.6b00376
• 作为产物：
  描述：

  2-甲基苯甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 以55.95%的产率得到2-methylpropane-2-sulfinic acid [1-(2-methyl-1-ylphenyl)ethylidene]amide
  参考文献：
  名称：

  Studies on Diastereofacial Selectivity of a Chiral tert-Butanesulfinimines for the Preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the Synthesis of Repaglinide

  摘要：

  一种新的不对称合成方法，用于合成一系列手性胺，包括(S)-3-methyl-1-(2-piperidin-1-yl-phenyl)butylamine (2a)，这是制备抗糖尿病药物瑞格列奈的关键中间体，采用Ellman试剂叔丁基亚砜胺。通过对叔丁基亚砜胺进行立体选择性的有机金属试剂加成，随后进行酸性和碱性处理。获得的手性胺通过核磁共振(NMR)、质谱(MS)及其他分析数据进行了表征。

  DOI：

  10.14233/ajchem.2013.15539

文献信息

• Unprecedented Copper(I) Bifluoride Complexes: Synthesis, Characterization and Reactivity
  作者：Thomas Vergote、Fady Nahra、Alexandre Welle、Michel Luhmer、Johan Wouters、Nathalie Mager、Olivier Riant、Tom Leyssens

  DOI：10.1002/chem.201102655

  日期：2012.1.16

  demonstrated that copper(I) bifluorides are very efficient catalysts, which do not require any additional activating agent. The first Cu‐catalyzed diastereoselective allylation of (R)‐N‐tert‐butanesulfinyl aldimines was also established. The method enables efficient, simple and general synthesis of enantiomerically enriched homoallylic amines at room temperature in high yields.

  成为或不成为双氟化物：已开发出两种合成途径，从而获得了前所未有的N-杂环卡宾铜（I）双氟化物络合物（参见方案）。催化测试表明，氟化氢（I）是非常有效的催化剂，不需要任何其他活化剂。的第一Cu催化的非对映选择性烯丙基化（[R ）- ñ -叔-butanesulfinyl醛亚胺也被建立。该方法能够在室温下以高收率高效，简单和通用地合成对映异构体富集的均烯丙基胺。
• Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of <i>Aspidosperma</i> Alkaloids (−)-Aspidospermidine, (−)-Tabersonine, and (−)-Vincadifformine
  作者：Senzhi Zhao、Rodrigo B. Andrade

  DOI：10.1021/acs.joc.6b02551

  日期：2017.1.6

  Michael/Mannich route to the tetrahydrocarbazole (ABE) core of Aspidosperma alkaloids is described. The scope of this novel transformation was studied in terms of the nucleophilic component (i.e., N-sulfinyl metallodienamine) and the electrophilic component (i.e., Michael acceptor). The successful application of this methodology toward the concise total syntheses of classical indole alkaloids (−)-aspidospermidine

  描述了芳烃融合的多米诺骨牌迈克尔/曼尼希路线的开发和应用，将其与曲霉生物碱的四氢咔唑（ABE）核心结合使用。就亲核组分（即，N-亚磺酰基金属亚胺）和亲电组分（即，迈克尔受体）研究了该新型转化的范围。还讨论了该方法在10-11个步骤中分别分别成功合成简明的吲哚生物碱（-）-aspidospermidine，（-）-tabersonine和（-）-vincadifformine的简明总合成方法。
• Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
  申请人：Arasappan Ashok

  公开号：US09433621B2

  公开（公告）日：2016-09-06

  The present invention provides compounds of Formula (I): and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19 and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing diseases or disorders such as viral infections and virus-related disorders.

  本发明提供了式(I)的化合物：以及所述化合物的互变异构体、异构体和酯，以及所述化合物的药学上可接受的盐、溶剂化合物和前药，其中R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n中的每个都是独立选择并如本文所定义。还提供了包含这些化合物的组合物。本发明的化合物作为HCV的抑制剂是有效的，并且在治疗或预防病毒感染和与病毒相关的疾病或紊乱方面，单独或与其他治疗剂一起使用是有用的。
• [EN] SUBSTITUTED PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS<br/>[FR] DÉRIVÉS DE PYRIDINE ET PYRIMIDINE SUBSTITUÉES ET LEUR UTILISATION DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：SCHERING CORP

  公开号：WO2010022121A1

  公开（公告）日：2010-02-25

  The present invention provides compounds of Formula (I): and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19 and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing diseases or disorders such as viral infections and virus-related disorders.

  本发明提供了式(I)的化合物：以及所述化合物的互变异构体、同分异构体和酯，以及所述化合物的药学上可接受的盐、溶剂化合物和前药，其中R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n中的每个均独立选择并如本文所定义。还提供了包含这些化合物的组合物。本发明的化合物作为HCV的抑制剂是有效的，并且在治疗或预防病毒感染和与病毒相关的疾病或紊乱方面，单独或与其他治疗剂一起使用是有用的。
• Asymmetric addition of benzothiazole to N-tert-butanesulfinyl imine for the synthesis of chiral α-branched heteroaryl amines
  作者：Jinlong Zhang、Yuhong Yang、Mei Wang、Li Lin、Rui Wang

  DOI：10.1016/j.tetlet.2012.09.131

  日期：2012.12

  This work concerns the asymmetric additions of benzothiazole to a variety of N-tert-butanesulfinyl imines with excellent diastereoselectivities (d.r. up to >99:1). Amino alkoxyl lithium was the key additive to obtain the excellent diastereoselectivity. More functionalized 4-methyl-5-vinyl thiazole and alkyl imines which can isomerize to enamines are also compatible substrates to the present protocol

  这项工作的关注苯并噻唑的不对称添加到各种ñ -叔-butanesulfinyl亚胺具有优良的非对映选择性（DR高达> 99：1）。氨基烷氧基锂是获得优异非对映选择性的关键添加剂。可以异构化成烯胺的更多官能化的4-甲基-5-乙烯基噻唑和烷基亚胺也是本方案的相容底物。